Method for producing oxadiazolinone compound and intermediate thereof

ABSTRACT

A compound represented by the formula (1): 
                         
wherein Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, Ar′ represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R represents an alkyl group having 1 to 4 carbon atoms.

TECHNICAL FIELD

The present invention relates to a method for producing anoxadiazolinone compound and an intermediate thereof.

BACKGROUND ART

As a method for producing an oxadiazolinone compound, there is known amethod in which a 2-aryl-substituted hydrazinecarboxylic acid methylester is treated with phosgene to give a2-(chlorocarbonyl)-2-aryl-substituted hydrazinecarboxylic acid methylester, which is then cyclized by the action of a base (for example,refer to JP-B-60-19302). However, such a method uses phosgene havingstrong toxicity, which requires facilities provided with safety measuresfor industrial practice.

DISCLOSURE OF THE INVENTION

Thus, the present inventors have developed a method for producing anoxadiazolinone compound without using phosgene having strong toxicity,thus accomplishing the present invention.

That is, the present application provides the following inventions.

[1] A compound represented by the formula (1):

wherein Ar and Ar′ each independently represents an aromatic hydrocarbongroup having 6 to 20 carbon atoms which may have a substituent, and Rrepresents an alkyl group having 1 to 4 carbon atoms.[2] The compound according to [1], wherein Ar is a phenyl group, and Ar′is a phenyl group which has an alkoxy group having 1 to 4 carbon atoms.[3] The compound according to [1], wherein Ar is a phenyl group, Ar′ isa 2-methoxyphenyl group, and R is a methyl group.[4] A method for producing an oxadiazolinone compound represented by theformula (2):

wherein Ar′ and R have the same meanings as defined below, whichcomprises step I of reacting a compound represented by the formula (3):

wherein Ar′ represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent, and R represents an alkylgroup having 1 to 4 carbon atoms, with a compound represented by theformula (4):ClCO₂Ar  (4)wherein Ar represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent; and step 11 of reacting acompound represented by the formula (1):

wherein Ar and Ar′ each independently has the same meaning as definedabove, which is obtained by step I, with a strong base.[5] A method for producing an oxadiazolinone compound represented by theformula (2):

wherein Ar′ and R have the same meanings as defined below, whichcomprises a step of reacting a compound represented by the formula (1):

wherein Ar and Ar′ each independently represent an aromatic hydrocarbongroup having 6 to 20 carbon atoms which may have a substituent, and Rrepresents an alkyl group having 1 to 4 carbon atoms, with a strongbase.[6] The method according to [4] or [5], wherein the strong base isselected from the group consisting of an alkali metal hydride, an alkalimetal amide compound, and an alkali metal hydroxide.[7] A method for producing a compound represented by the formula (1):

wherein Ar, Ar′ and R have the same meanings as defined below, whichcomprises a step of reacting a compound represented by the formula (3):

wherein Ar′ represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent, and R represents an alkylgroup having 1 to 4 carbon atoms, with a compound represented by theformula (4):ClCO₂Ar  (4)wherein Ar represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent.[8] The method according to [4], [5] or [7], wherein Ar is a phenylgroup, and Ar′ is a phenyl group which has an alkoxy group having 1 to 4carbon atoms.[9] The method according to [4], [5] or [7], wherein Ar is a phenylgroup, Ar′ is a 2-methoxyphenyl group, and R is a methyl group.

EFFECTS OF THE INVENTION

According to the present invention, it is possible to produce anoxadiazolinone compound industrially easily without requiring specialfacilities since phosgene having strong toxicity is not used.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

The compound of the present invention (hereinafter, this compound issometimes referred to as a “compound (1)”) is represented by thefollowing formula (1).

In the present description, Ar represents an aromatic hydrocarbon grouphaving 6 to 20 carbon atoms which may have a substituent.

In the present description, examples of the aromatic hydrocarbon groupinclude a phenyl group and a naphthyl group.

Examples of the substituent in the aromatic hydrocarbon group includealkyl groups having 1 to 6 carbon atoms, such as a methyl group, anethyl group, a propyl group, an isopropyl group, a butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group,and a hexyl group; haloalkyl groups having 1 to 6 carbon atoms, such asa fluoromethyl group and a trifluoromethyl group; alkoxy-substitutedalkyl groups having 1 to 10 carbon atoms, such as a methoxymethyl group,an ethoxymethyl group, and a methoxyethyl group; alkoxy groups having 1to 6 carbon atoms, such as a methoxy group, an ethoxy group, a propoxygroup, an isopropoxy group, a butoxy group, an isobutoxy group, asec-butoxy group, a tert-butoxy group, and a pentyloxy group; haloalkoxygroups having 1 to 6 carbon atoms, such as a fluoromethoxy group and atrifluoromethoxy group; alkoxy-substituted alkoxy groups having 2 to 10carbon atoms, such as a methoxymethoxy group, an ethoxymethoxy group,and a methoxyethoxy group; halogen atoms such as a fluorine atom and achlorine atom; a nitro group; cycloalkyl groups having 3 to 6 carbonatoms, such as a cyclopentyl group; and cycloalkyloxy groups such as acyclopentyloxy group.

Specific examples of Ar include a phenyl group, an alkyl-substitutedphenyl group, a halogen-substituted phenyl group, and analkoxy-substituted phenyl group, and more specific examples thereofinclude a 2-methylphenyl group, a 4-chlorophenyl group, a 4-methylphenylgroup, and a 2-methoxyphenyl group.

In the present description, Ar′ represents an aromatic hydrocarbon grouphaving 6 to 20 carbon atoms which may have a substituent.

Specific examples of Ar′ include a phenyl group, an alkyl-substitutedphenyl group, a halogen-substituted phenyl group, and analkoxy-substituted phenyl group, and more specific examples thereofinclude a 2-methylphenyl group, a 4-chlorophenyl group, a 4-bromophenylgroup, and a 2-methoxyphenyl group.

In the present description, R represents an alkyl group having 1 to 4carbon atoms.

Examples of the alkyl group represented by R include a methyl group, anethyl group, a n-propyl group, an isopropyl group, a n-butyl group, anda t-butyl group.

As described above, the compound (1) has a structure represented by theformula (1) and therefore it can be easily converted into a compound(2). Accordingly, the compound (1) is useful as an intermediate in theproduction of the compound (2).

The compound (1) is preferably a compound of the formula (1) in which Aris a phenyl group, and Ar′ is a phenyl group which has an alkoxy grouphaving 1 to 4 carbon atoms, and more preferably a compound of theformula (1) in which Ar is a phenyl group, Ar′ is a 2-methoxyphenylgroup, and R is a methyl group.

Examples of the compound (1) include1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl) hydrazine,1-methoxycarbonyl-2-(4-nitrophenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine,1-methoxycarbonyl-2-(4-chlorophenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine,1-(2-fluorophenoxycarbonyl)-1-(2-methoxyphenyl)-2-methoxycarbonylhydrazine,1-methoxycarbonyl-2-(4-methylphenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine,1-methoxycarbonyl-2-(2-methoxyphenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine,1-methoxycarbonyl-2-(4-trifluoromethylphenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(4-methylphenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(4-chlorophenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(4-chlorophenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(2-fluorophenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(4-bromophenyl)hydrazine, 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(4-nitrophenyl)hydrazine, 1-ethoxycarbonyl-2-phenoxycarbonyl-2-phenylhydrazine,1-ethoxycarbonyl-2-(phenoxycarbonyl)-2-(2-methoxyphenyl) hydrazine,1-(phenoxycarbonyl)-1-(2-methoxyphenyl)-2-propoxycarbonylhydrazine,1-methoxycarbonyl-2-(phenoxycarbonyl)-2-phenylhydrazine,1-(4-chlorophenoxycarbonyl)-1-phenyl-2-methoxycarbonylhydrazine,1-butoxycarbonyl-2-(2-fluorophenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine, and 1-butoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl)hydrazine.

The compound (1) can be produced by an operation of step I describedhereinafter.

The method for producing an oxadiazolinone compound of the presentinvention include step I of reacting a compound represented by theformula (3) (hereinafter sometimes referred to as a compound (3)) with acompound represented by the formula (4) (hereinafter sometimes referredto as a compound (4)) and step II of reacting the compound (1) obtainedby step I with a strong base.

The method for producing the compound (1) including step I, and themethod for producing the oxadiazolinone compound (hereinafter sometimesreferred to as a compound (2)) including step II are also one of thepresent invention.

In the present description, a compound (3) is represented by the formula(3):

wherein Ar′ and R are as respectively defined above.

Examples of the compound (3) include 1-(C1-C4alkoxy)carbonyl-2-phenylhydrazine, 1-(C1-C4 alkoxy)carbonyl-2-[(C1-C4alkoxy)phenyl] hydrazine, and 1-(C1-C4alkoxy)carbonyl-2-halophenylhydrazine, and more specific examplesthereof include 1-methoxycarbonyl-2-phenylhydrazine,1-ethoxycarbonyl-2-phenylhydrazine,1-methoxycarbonyl-2-(2-methoxyphenyl) hydrazine,1-methoxycarbonyl-2-(4-methylphenyl) hydrazine,1-methoxycarbonyl-2-(4-chlorophenyl) hydrazine,1-ethoxycarbonyl-2-(4-methoxyphenyl) hydrazine,1-methoxycarbonyl-2-(2-fluorophenyl) hydrazine,1-methoxycarbonyl-2-(4-nitrophenyl) hydrazine,1-ethoxycarbonyl-2-(2-methoxyphenyl) hydrazine,1-(2-methoxyphenyl)-2-propoxycarbonylhydrazine, and1-butoxycarbonyl-2-(2-methoxyphenyl) hydrazine.

As the compound (3), a commercially available product may be used, orthose produced by the method described in JP-B-60-19302 or the like,that is, a method of reacting phenylhydrazine with a compoundrepresented by ClCO₂R may be used.

In the present description, the compound (4) is represented by theformula (4):ClCO₂Ar  (4)wherein Ar is as defined above.

Examples of the compound (4) include phenyl chloroformate,(nitro-substituted phenyl)chloroformate, (halogen-substitutedphenyl)chloroformate, (C1-C4 alkyl-substituted phenyl)chloroformate,(C1-C4 alkoxy-substituted phenyl)chloroformate, and (C1-C4haloalkyl-substituted phenyl)chloroformate, and more specific examplesthereof include phenyl chloroformate, (4-nitrophenyl)chloroformate,(4-chlorophenyl)chloroformate, (2-fluorophenyl)chloroformate,(4-methylphenyl) chloroformate, (2-methoxyphenyl)chloroformate, and(4-trifluoromethylphenyl)chloroformate.

As the compound (4), a commercially available product may be used, orthose produced by a known method described in Tetrahedron, 58, 10011(2002) or the like may be used.

In step I, the use amount of the compound (4) may be 1 mol or more,usually from 1 to 10 mol, and preferably from 1 to 3 mol, per mol of thecompound (3).

In the reaction of step I, it is preferred to optionally use a base. Itis possible to neutralize hydrogen chloride produced as a by-product inthe reaction by using the base.

Any of an organic base and an inorganic base can be used as such a base.

Examples of the organic base include tertiary amines such astriethylamine, trioctylamine, and diisopropylethylamine;nitrogen-containing aromatic compounds such as pyridine and imidazole;and alkali metal alkoxides such as sodium methoxide and sodium ethoxide.

Examples of the inorganic base include carbonates of alkali metals oralkali earth metals, such as lithium carbonate, sodium carbonate,potassium carbonate, cesium carbonate, magnesium carbonate, and calciumcarbonate; hydrogen carbonates of alkali metals or alkali earth metals,such as lithium hydrogencarbonate, sodium hydrogencarbonate, potassiumhydrogencarbonate, cesium hydrogencarbonate, magnesiumhydrogencarbonate, and calcium hydrogencarbonate; hydroxides of alkalimetals or alkali earth metals, such as lithium hydroxide, sodiumhydroxide, potassium hydroxide, cesium hydroxide, magnesium hydroxide,and calcium hydroxide; and any mixtures thereof. Carbonates of alkalimetals or alkali earth metals are preferred.

The use amount of the base may be 1 mol or more per mol of the compound(4), which is usually within the range from 1 to 3 mol although there isno particular upper limit.

The reaction of step T is usually carried out in the presence of anorganic solvent. Examples of the organic solvent include ether solventssuch as methyl tert-butyl ether, tetrahydrofuran, dimethoxyethane, anddiglyme; nitrile solvents such as acetonitrile and propionitrile; andaromatic hydrocarbon solvents such as toluene and xylene.

There is no particular limitation on the use amount of the organicsolvent. Taking volume efficiency into consideration, the use amount ofthe organic solvent is usually 0.5 parts by weight or more and 100 partsby weight or less per part by weight of the compound (3), from theviewpoint of practical use.

The reaction temperature is usually within the range from −20 to 200°C., and preferably from 0 to 100° C.

In the reaction of step I, it is preferred that the compound (3), anorganic solvent and, if necessary, a base are mixed in any order and acompound (4) is added to the obtained mixture.

The reaction is usually carried out under a normal pressure condition.Proceeding of the reaction can be confirmed by conventional analysismeans such as gas chromatography, high-performance liquidchromatography, thin-layer chromatography, NMR, and IR.

After completion of the reaction, the compound (1) can be isolated fromthe mixture by means such as crystallization, filtration, distillation,and extraction. The isolated compound (1) may be further purified, forexample, by conventional purification means such as rectification andcolumn chromatography.

Next, step II of reacting the compound (1) with a strong base will bedescribed.

Examples of the strong base include alkali metal hydrides such aslithium hydride, sodium hydride, and potassium hydride; alkali metalamide compounds such as lithium amide, sodium amide, and potassiumamide; and alkali metal hydroxides such as lithium hydroxide, sodiumhydroxide, and potassium hydroxide. Alkali metal hydrides and alkalimetal hydroxides are preferable, and sodium hydride and potassiumhydroxide are more preferable.

The use amount of the strong base may be usually 0.8 mol or more per molof the compound (1), which is preferably within the range from 0.8 to 3mol although there is no particular upper limit.

The reaction of step II is usually carried out in the presence of anorganic solvent. Examples of the organic solvent include ether solventssuch as methyl tert-butyl ether, tetrahydrofuran, dimethoxyethane, anddiglyme; nitrile solvents such as acetonitrile and propionitrile; andaromatic hydrocarbon solvents such as toluene and xylene. There is noparticular limitation on the use amount of the organic solvent. Takingvolume efficiency into consideration, the use amount of the organicsolvent is usually 0.5 parts by weight or more and 100 parts by weightor less per part by weight of the compound (1), from the viewpoint ofpractical use.

The reaction temperature is usually within the range from −20 to 100°C., and preferably from −20 to 50° C.

In the reaction of step II, the compound (1) and an organic solvent maybe mixed and a strong base may be added to the obtained mixture, or astrong base and an organic solvent may be mixed and the compound (1) maybe added to the obtained mixture, or the compound (1) and a strong basemay be simultaneously added to an organic solvent. It is preferred thata strong base and an organic solvent are mixed and the compound (1) isadded to the obtained mixture.

The reaction of step II is usually carried out under normal pressureconditions. Proceeding of the reaction can be confirmed by conventionalanalysis means such as gas chromatography, high-performance liquidchromatography, thin-layer chromatography, NMR, and IR.

After completion of the reaction, the compound (2) can be isolated fromthe mixture by means such as crystallization, filtration, distillation,and extraction. The isolated compound (2) may be further purified byconventional purification means such as rectification and columnchromatography.

Examples of the compound (2) include5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one,5-ethoxy-3-phenyl-1,3,4-oxadiazolin-2-one,5-methoxy-3-(4-methylphenyl)-1,3,4-oxadiazolin-2-one,5-methoxy-3-(4-chlorophenyl)-1,3,4-oxadiazolin-2-one,5-ethoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one,5-methoxy-3-(2-fluorophenyl)-1,3,4-oxadiazolin-2-one,5-methoxy-3-(4-bromophenyl)-1,3,4-oxadiazolin-2-one, and5-methoxy-3-(4-nitrophenyl)-1,3,4-oxadiazolin-2-one, and5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one is preferable.

EXAMPLES

The present invention will be described in more detail by Examples asfollow, but the present invention is not limited to these Examples.

Example 1 (Step I-1) Preparation of Compound (1)

In a nitrogen-substituted 100 ml flask, 2.0 g of1-methoxycarbonyl-2-(2-methoxyphenyl)hydrazine, 7.0 g of potassiumcarbonate and 50 g of acetonitrile were charged, and 8.0 g of phenylchloroformate was added dropwise at room temperature under stirring over1 hour, and then the mixture was stirred at the same temperature for 7hours. The inorganic salt precipitated from the obtained reactionmixture was filtered and then acetonitrile was distilled off. When 5 gof ethyl acetate and 10 g of n-hexane were added to the residue, acrystal was precipitated. The precipitated crystal was filtered anddried to obtain 3.0 g of a pale yellow crystal.

As a result of analysis by ¹H-NMR, the crystal was identified as1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl) hydrazine.Yield: 93%.

¹H-NMR (δppm, CDCl₃, TMS standard): 3.74 (s, 3H), 3.88 (s, 3H), 6.9-7.42(m, 9H), 7.65 (bs, 1H)

(Step II-1) Preparation of Compound (2)

In a nitrogen-substituted 50 ml flask, 92 mg of1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl) hydrazinesynthesized in step I-1 and 2 g of acetonitrile were charged and cooledto 0° C., followed by the addition of 14 mg of sodium hydride (60% inparaffin liquid) under stirring and then stirring at the sametemperature for 1 hour. To the obtained reaction mixture, 10 g of ethylacetate and 10 g of water were added and the organic layer was analyzedby gas chromatography (internal standard method). As a result, the yieldof 5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one was 46%.

Example 2 (Step I-2) Preparation of Compound (1)

In a nitrogen-substituted 100 ml flask, 5.0 g of1-methoxycarbonyl-2-(2-methoxyphenyl) hydrazine, 3.9 g of triethylamineand 15 g of tetrahydrofuran were charged and 6.0 g of phenylchloroformate was added dropwise at room temperature under stirring over1 hour, and then the mixture was stirred at the same temperature for 2hours. To the obtained reaction mixture, 15 g of toluene and 15 g of a5% hydrochloric acid solution were added and, after stirring, themixture was allowed to stand, resulting in separation into two layers.Therefore, the aqueous layer as the lower layer was separated. In thesame manner, the oil layer was washed once with 15 g of a 5%hydrochloric acid solution, washed once with 15 g of water andconcentrated, and then 10 g of ethyl acetate and 20 g of n-hexane wereadded to the residue. As a result, a crystal was precipitated. Theprecipitated crystal was filtered and dried to obtain 7.7 g of a paleyellow crystal. As a result of analysis by ¹H-NMR, the crystal wasidentified as 1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl)hydrazine. Yield: 96%.

(Step II-2) Preparation of Compound (2)

In a nitrogen-substituted 50 ml flask, 200 mg of sodium hydride (60% inparaffin liquid) and 5 g of acetonitrile were charged and cooled to 0°C. To this mixed solution, 1 g of1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl) hydrazinesynthesized in step I-2 was dividedly added (each 50 mg) at the sametemperature under stirring over 30 minutes, followed by stirring at thesame temperature for 30 minutes. To the obtained reaction mixture, 10 gof toluene and 10 g of water were added and the organic layer wasanalyzed by gas chromatography (internal standard method). As a result,the yield of 5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one was28% and 72% of 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(2-methoxyphenyl)hydrazine as a raw material remained.

Example 3 Preparation of Compound (2)

In a nitrogen-substituted 50 ml flask, 300 g of1-methoxycarbonyl-2-phenoxycarbonyl-2-(2-methoxyphenyl) hydrazinesynthesized in Example 1 (step I-1) and 10 g of acetonitrile werecharged and cooled to 0° C., followed by addition of 64 mg of apotassium hydroxide powder under stirring and then stirring at the sametemperature for 1 hour. To the obtained reaction mixture, 10 g of ethylacetate and 10 g of water were added and the organic layer was analyzedby gas chromatography (internal standard method). As a result, the yieldof 5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazolin-2-one was 26% and 30%of 1-methoxycarbonyl-2-(phenoxycarbonyl)-2-(2-methoxyphenyl) hydrazineas a raw material was recovered.

Example 4 (Step I-3) Preparation of Compound (1)

In a nitrogen-substituted 100 ml flask, 500 mg of1-ethoxycarbonyl-2-phenylhydrazine, 420 mg of triethylamine and 5 g oftetrahydrofuran were charged and 650 mg of phenyl chloroformate wasadded dropwise at room temperature under stirring for 30 minutes, andthen the mixture was stirred at the same temperature for 2 hours. To theobtained reaction mixture, 10 g of toluene and 5 g of a 5% hydrochloricacid solution were added and, after stirring, the mixture was allowed tostand, resulting in separation into two layers. Therefore, the aqueouslayer as the lower layer was separated. In the same manner, the oillayer was washed once with 5 g of a 5% hydrochloric acid solution,washed once with 5 g of water and concentrated, and then 3 g of ethylacetate and 5 g of n-hexane were added to the residue. As a result, acrystal was precipitated. The precipitated crystal was filtered anddried to obtain 410 mg of a pale yellow crystal. As a result of analysisby ¹H-NMR, the crystal was identified as1-ethoxycarbonyl-2-phenoxycarbonyl-2-phenylhydrazin. Yield: 50%.

¹H-NMR (δppm, CDCl₃, TMS standard): 1.29 (t, 3H), 4.22 (q, 2H), 7.0-7.42(m, 10H)

(Step II-3) Preparation of Compound (2)

In a nitrogen-substituted 50 ml flask, 100 mg of1-ethoxycarbonyl-2-phenoxycarbonyl-2-phenylhydrazine synthesized in stepI-3 and 2 g of acetonitrile were charged and cooled to 0° C., followedby addition of 20 mg of sodium hydride (60% in paraffin liquid) understirring and then stirring at the same temperature for 1 hour. To theobtained reaction mixture, 10 g of ethyl acetate and 10 g of water wereadded and the organic layer was analyzed by gas chromatography (internalstandard method), and thus production of5-ethoxy-3-phenyl-1,3,4-oxadiazolin-2-one was confirmed.

INDUSTRIAL APPLICABILITY

According to the present invention, an oxadiazolinone compound can beproduced industrially easily without requiring special facilities.

1. A compound represented by the formula (1):

wherein Ar and Ar′ each independently represents an aromatic hydrocarbongroup having 6 to 20 carbon atoms which may have a substituent, and Rrepresents an alkyl group having 1 to 4 carbon atoms.
 2. The compoundaccording to claim 1, wherein Ar is a phenyl group, and Ar′ is a phenylgroup which has an alkoxy group having 1 to 4 carbon atoms.
 3. Thecompound according to claim 1, wherein Ar is a phenyl group, Ar′ is a2-methoxyphenyl group, and R is a methyl group.
 4. A method forproducing an oxadiazolinone compound represented by the formula (2):

wherein Ar′ and R have the same meanings as defined below, whichcomprises step I of reacting a compound represented by the formula (3):

wherein Ar′ represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent, and R represents an alkylgroup having 1 to 4 carbon atoms, with a compound represented by theformula (4):ClCO₂Ar  (4) wherein Ar represents an aromatic hydrocarbon group having6 to 20 carbon atoms which may have a substituent; and step 11 ofreacting a compound represented by the formula (1):

wherein Ar and Ar′ each independently has the same meaning as definedabove, which is obtained by step I, with a strong base.
 5. A method forproducing an oxadiazolinone compound represented by the formula (2):

wherein Ar′ and R have the same meanings as defined below, whichcomprises a step of reacting a compound represented by the formula (1):

wherein Ar and Ar′ each independently represent an aromatic hydrocarbongroup having 6 to 20 carbon atoms which may have a substituent, and Rrepresents an alkyl group having 1 to 4 carbon atoms, with a strongbase.
 6. The method according to claim 4 or 5, wherein the strong baseis selected from the group consisting of an alkali metal hydride, analkali metal amide compound, and an alkali metal hydroxide.
 7. A methodfor producing a compound represented by the formula (1):

wherein Ar, Ar′ and R have the same meanings as defined below, whichcomprises a step of reacting a compound represented by the formula (3):

wherein Ar′ represents an aromatic hydrocarbon group having 6 to 20carbon atoms which may have a substituent, and R represents an alkylgroup having 1 to 4 carbon atoms, with a compound represented by theformula (4):ClCO₂Ar  (4) wherein Ar represents an aromatic hydrocarbon group having6 to 20 carbon atoms which may have a substituent.
 8. The methodaccording to claim 4, 5 or 7, wherein Ar is a phenyl group, and Ar′ is aphenyl group which has an alkoxy group having 1 to 4 carbon atoms. 9.The method according to claim 4, 5 or 7, wherein Ar is a phenyl group,Ar′ is a 2-methoxyphenyl group, and R is a methyl group.